Black Bras & Strappy High Heeled Shoes
by Tidia
Summary: Mentioned in Ridley's Great, Beautiful, Terrible Things. Caleb takes Dean on the ultimate field trip. John is not happy. Warnings for language & topic.


**Black Bras & Strappy High Heeled Shoes**

**Official disclaimer: I, Tidia, in no way condone underage drinking or pre-marital teen sex, but it is TOTALLY something a big brother would do. And Ridley, school psychologist, says it is an unfortunate fact that a lot of boys lose their virginity BEFORE 15. **

**Author's Note: I had technical difficulties putting this up so I had to change the title…very strange. Well, this morphed from one fic, to this fic, and a conversation with Ridley about how Dean had to have someone in his life as an influence other than John. So, it is Caleb, and I borrowed Ridley's Caleb. Mog did a quick beta for me. I hope you all enjoy it.**

July in Mississippi was sweltering. The air conditioner worked all day to bring the temperature in the rented home to a comfortable seventy-five degrees. There was a perpetual film of sweat on each of the Winchester men. Their host, Caleb Reaves, reveled in the hot weather, but even he was finding the southern heat stifling.

Summers for the Winchesters were spent on the road from one ghost hunt to another. The boys were out of school, and John enjoyed the freedom away from a rigid schedule. Caleb had 'entertained' guests for the last week, needing assistance to bring about the demise of a Chimera. The monster with the body of a goat, the tail of a dragon and the head of a lion had the ability to breathe fire, which made it more than a one hunter job. But, he was looking forward to the end of the gig. There was not a manual entitled, 'The Care and Feeding of the Winchesters,' and Caleb soon realized that adolescents wanted to eat all the time.

They had returned from the swamp area near Soso, Mississippi, having lost sight of the Chimera. John was pensive, formulating a new attack. Caleb went to the refrigerator, looking forward to a nice cold beer, deferring to the older hunter. He moved around the bottles, jars and plastic wrapping to no avail. There was no beer, not even a bottle of wine. Part of the Winchester manual would have to include a chapter on John and his requirement of spirits of another sort.

He had tossed the keys to his Jeep on the dining room table upon arrival. Now, he scooped them up, and kept the momentum to the door. Sam sat watching Teenage Mutant Ninja Turtles, Dean was next to him with his feet on the coffee table tabbing through a well worn _Car and Driver_.

"Where are you going?" John asked, looking up from his notes.

"Beer run," Caleb replied, shifting the keys from his right hand to his left.

Dean tossed the magazine, the pages fanning out on the couch. "I'm coming," he announced. He glanced over at his father and received a nod.

Caleb raised an eyebrow. "I didn't know I invited you."

"Yeah, but you were _thinking_ it." The young man grabbed his baseball cap and placed it low, over his eyes.

"Can I go too?" The eleven-year-old raised his eyes away from the television.

"Daaadddd," Dean whined, craving time away from his tag-a-long little brother.

"Don't whine, Dean or else no one is going." Reaves had his hand on the door knob ready to exit without any entourage. But, John had other plans. "No, Sam, you can stay home with me." Caleb saw Sam roll his eyes, and choked off a laugh. The boys' father was not known to be engaging company.

"I'll be back later, Sammy." The youngest Winchester raised his middle finger in acknowledgement.

The humidity of the outside air hit the two with full force. Caleb could feel his jeans sticking to him. His dark hair was caught up in a pony tail, keeping his neck cool, but it wasn't enough. The Jeep lacked air conditioning, getting moving and creating a breeze was the only option. Dean settled into the passenger seat.

Caleb had been looking forward to the drive alone. However, he considered Dean his protégé, and therefore hazing was a requirement. It would make the drive lively. "So, Deuce you getting any action?"

At fifteen, Dean was 5'9" and not done growing if John's stature was the measuring stick. Caleb could sense the young man's embarrassment.

"It's Dean, and the answer is enough." Dean answered, shifting in his seat.

Reaves gave a low whistle. "Yeah, tenth grade must be a hot bed."

The young man remained silent for the remaining ten minute ride. Caleb pulled into the lot, turning off the ignition. He held the keys up and placed them in his jean pocket. "I know what you're thinking, before you even think it."

Dean frowned, looking at the older hunter in confusion. "That demon blood making you insane or something?"

Caleb snorted. He knew what he would have done at the teen's age, and assumed Dean would do the same. "Like you wouldn't take the Jeep for a joy ride and leave me."

The younger man nodded, contemplating the idea that hadn't previously occurred to him. "I was going to do that tomorrow."

"Exactly," Reaves replied as he hopped out of the Jeep.

"Hey, Demon Spawn," Dean yelled out, "Get some Jose too."

Caleb laughed at the audacity of the teenager to give him an order. "Yeah, right."

"Seriously," Dean threw his baseball hat at the older hunter, hitting him in the face in order to get his attention. "You just get beer and Dad will go through it like water. A little tequila and you'll be able to have a Miller time for yourself."

Reaves confiscated the beat-up Red Sox hat, pulling it over his own head. "You know, kid, sometimes you're smart."

"And always handsome." Dean crossed his arms and reclined back into the bucket seats.

Two cold six packs and two bottles of tequila later, Caleb and Dean were back on the road. The teen immediately snatched back his baseball hat. He studied it for a moment before placing it over his buzz cut hair.

"I don't have cooties," Caleb said.

"Cooties? Dude, grow up." Dean snorted, moving his head to the right so he could catch the breeze caused by the vehicle's momentum.

They drove along the two-lane road to return to the rented house. Red, shining, string-along lights caught Caleb's attention. The Red Caboose was the only bar within twenty miles. Since being in the small, backwater town, Reaves had become a regular. He had already passed the building when the idea struck him. The hunter checked the road before executing a u-turn.

Dean gripped the dash board. "What the hell?"

Caleb didn't reply as he pulled into the gravel lot, parking behind the well worn building. He had taught the boy to cuss and play cards while his father taught him pool hustling and demon hunting. The older hunter wanted to make the summer of 1995 memorable for the teen. The milestones in the kid's life had nothing to do with growing up and everything to do with the supernatural. It was time for something special - birthday and Christmas all wrapped up in one.

"Why are we here?" The teen asked, looking at a dumpster that sat against the structure.

"The women in there are gonna give you the keys to the kingdom." Caleb smiled, stretching over and opening the glove compartment. He pulled out some foil packets, and laid open his hand for Dean to see.

The young man looked at the offering and then at his friend once more. "Condoms?"

Reaves held one up. "Yep."

"All right!" Grasping the hunter's gift. Dean grabbed one of the foil packets and studied it. "What, you don't have the magnum size?"

Caleb frowned at the teen's retort. "Hey! You wanna do this or what?" He received a nod. The glove compartment was open and Reaves was about to replace the remaining condoms when Dean snatched another one.

The teen shrugged his shoulders. "The one in my wallet is kinda old."

Caleb shook his head at the boldness of the young man. He took in a deep breath, and let it out slowly. John was going to be livid. He would figure it out eventually, and Caleb didn't know if he wanted to be on the hunter's bad side. "Should I be doing this?"

"Hell, yeah!" The teen replied excitedly.

Nervously, Caleb tugged on his pony tail, feeling the humidity dampening his hair. "That wasn't directed to you."

Dean sensed that he was about to lose the opportunity of a lifetime. He placed his hand on the other hunter's arm. "You're like Ben Kenobi, passing on the ways of the Force. . ."

Caleb laughed. He was about to take a kid who was still into Star Wars to lose his virginity. He nodded in agreement with Dean. He was still into Star Wars too, although he didn't know if he wanted to be compared to the dead Jedi Master. He had always considered himself a Han Solo kind of guy. "Okay, Deuce, I'm going to give you some advice so the bees come to the honey." He paused to make sure the teen was listening. Satisfied, he continued. "You need to be an equal opportunity guy - blonde, red-head, brunette it doesn't matter. . ."

"But blondes. . ." Dean interjected, licking his lips.

The hunter shook his head. "Doesn't make a difference, you look for a black bra and strappy, high heeled shoes. Those women, they are feeling good, and you want to make them feel even better."

"Black bra, strappy shoes - got it," Dean jumped out of the Jeep.

Caleb got out slowly. The teen was having an adrenaline rush. The dark haired man had witnessed the reaction before, after hunts. "They know me at this bar. You need to act twenty-one." The teen squared off his shoulders and removed the grin from his face. He looked older. Dean didn't have the luxury to be gawky. The teen needed his body to perform; he needed to rely on it during hunts. In temperament, the kid was more grown up than his father, taking the responsibility of raising Sam.

They entered the bar, and Caleb got a welcoming nod from the bartender. An old '80's tune was playing in the background. There was a light crowd for the early night hour, but it was midweek. Caleb held up his hand, gesturing for two beers, and ushered Dean to the dark corner table where he wouldn't draw attention to himself. Reaves left the teen at the table, while he fetched the beers from the bartender. Two Budweisers were waiting for him. Caleb placed a ten dollar bill on the glass covered counter top.

He gestured to the girl in the corner who he had become acquainted with upon his arrival in town. He stared at her as she walked over, a friend in tow. Her name escaped him. Briefly, he touched her mind. Mac would say that he had breached some ethical duty of psychics, but Caleb applied the cafeteria doctrine to his adopted father's lessons; he chose which ones worked for him, and those that didn't.

Dean was studying the bar's lack of ambience, enthralled with an old black and white picture of a tractor. The teen perked up when he saw Caleb returning with two petite blondes and the drinks.

"These are some friends of mine. Karen," Caleb gestured to a girl who had her hand possessively on the hunter's arm. "And Stella. This is my brother, Dean." The teen stood up, and pulled out a chair for Stella. Karen took a seat next to Reaves.

"I didn't know you had a brother." She looked at Caleb with a big smile of promises and inferences that they knew each other well.

The older hunter took a swig from his beer, feeling the icy coolness go down his throat. "Yep, there's Bobby, me and Dean."

"Hey," she said too loudly, drawing the attention of the rag tag patrons for a moment. "B, C, D, what happened to A?"

Caleb slowly grinned, and watched as Dean lifted the beer to his lips. "Yeah, it's actually John, bastard son."

The teen began to cough, putting the beer down to cover his smile at his father's expense.

Reaves continued the insult. "Addle brained too. We don't like to talk about him."

Karen brought the corner of her lips down to an exaggerated sad face, "Sorry."

Dean stared at his companion. Stella was a well-endowed woman, her black bra peeking out. His eyes kept drifting to her breasts. He smiled at her, looking into her eyes with all seriousness. "You must be a model. You look like Claudia Schiffer." The teen leaned back in his chair, lifting the front legs off the floor, giving himself enough of a view to see Stella's shoes. She was wearing black, strappy, high-heeled shoes plus the black bra. Dean knew he was going to get lucky tonight. So caught up in the thought he teetered on the chair, almost falling before bringing the chair forward with a hard thump.

Stella giggled, and flipped her shoulder length platinum blonde hair back. "No, I work as a cashier at the pharmacy."

The hair flip was all the encouragement Dean needed. The three beers helped too. Caleb overheard snippets of the conversation, and shook his head at the bravado behind lies.

"Two years in the Marines."

"Ohh, the Marines. . ."

"Got the scars to prove it."

"Can I see them?"

"Maybe later."

Dean gave a quick glance over to Caleb. The older hunter understood it to be a signal. The teen was ready to make his move. Suddenly, Reaves felt pride. He had influenced Dean's confidence in women, especially one seven years older. "You wanta dance?" Caleb heard the teen ask.

Bon Jovi's _Wanted Dead or Alive_ played on the juke box. There was another couple dancing on the uneven, pine wood floor. Dean brought the girl in close, one arm wrapped around her neck and the other holding a beer as he kissed her. She molded her body against him. Before the end of the song, he was leading her out the door.

Forty-five minutes later Dean reappeared, without his baseball cap, but with a wide smile showing his rapture. He held Stella close.

Caleb glanced at his watch. The two hunters had been gone for hours. Reaves would have to write a work of fiction if they were going to come away unscathed from facing John Winchester. "You ready to go?"

Dean lifted his finger, gesturing he needed one more minute. He scooped Stella in his arms and gave her a deep kiss. The platinum blonde nervously pushed her hair off her face. "Call me," she mouthed. "Soon."

Reaves guided his charge out the door and to the Jeep. Happiness and a goofy smile made Dean shine under the night sky.

"I love this Jeep. How she stretched over ...Man, she was flexible. I love this roll bar. You know I think I want to marry her." The teenager rambled on, reaching to touch the roll bar.

Caleb laughed, wondering if Dean would be able to rein in his emotions before they reached home base. "Alabama is a county away. But, she might have a problem with the age difference."

"I didn't hear her complaining." Dean retrieved his baseball cap from the backseat, and placed it low on his head. "Plus, she'd only be the first Mrs. Winchester."

"The first?" Reaves snorted, as he turned the vehicle onto the road.

"Yeah, I mean I am not a one woman man." Dean rubbed his chest.

"You don't have to marry them all, Dean." Caleb rolled his eyes at the teen's misinformation. The statement seemed to reflect the religious man in the brotherhood. "Pastor Jim is just making that shit up about burning in hell."

Dean tipped the brim of his baseball hat up. "No, I was thinking about what Bobby said."

Caleb slowed down so he was within the posted speed limit and glanced at the teen. "Don't ever listen to Bobby. The guy looks like Cooter and has a blow up doll in the closet."

The young man chuckled heartily. Reaves couldn't remember the last time, if ever, that Dean was so uncollected.

"Thanks Caleb." The teenager sighed.

Reaves gave a slight nod, and pressed down on the gas pedal again. He looked out at the endless road ahead. "Yeah, you're the annoying brother I never really wanted," he admitted.

"So," Dean looked away from Caleb, but his words still could be picked up on the wind, "Sam's turn in 4 years."

"Nope," Reaves replied. A piece of his hair had gotten lose from the elastic, and danced in front of his face. "It's a job for a brother."

The teenager nodded. "So what's Sam to you?"

"My nerdy nephew," the older hunter replied. "You might want to wait until he's 17."

They both laughed. Dean stood up in the Jeep, his arms out wide as he yelled out to the sleeping town. "WOOHOO!"

And Caleb laughed at the teen's joy. He was happy and free with the big boys, and still young enough to collect fireflies with his brother. Reaves got caught up with the heady feeling that lasted until they saw John Winchester waiting on the porch of their rented home.

"Let me do all the talking. . ." he said quietly, as Dean got the now warm beer and tequila from the back seat. He handed one six pack and bottle to Caleb and carried the other one himself.

Unfortunately, Dean's cocky swagger was not helping the situation.

"Where have you been?" John growled, blocking the path to the door.

"Beer run." Caleb did not meet the Winchester patriarch's stare. He glanced down at his watch as if just noticing the time, but also using the turn of his wrist to show John the tequila. He hoped it would be a peace offering. "They ran out of beer so we had to fine another place."

"Ah-huh, not believing the bullshit," John took the beer and tequila from his son. He placed a hand on Dean's chest studying him. "Try again," he ordered his son.

"Hey, did Sammy go to bed?" The teen grinned at his father, trying to diffuse the situation.

John closed his eyes and wiped a hand down his face. Caleb knew the reaction meant they had been discovered. "Yeah, four hours ago," The older hunter took a step to the side to allow his son to pass. "Go to bed, we'll talk about this later."

The eldest Winchester watched his normally level headed son skip up the stairs. He shook his head. Gathering his anger again, he gestured to Reaves to follow him inside. John placed the beer on the kitchen table. He opened the bottle of tequila and took a drink. "Jesus, Caleb."

Reaves deposited his load on the table too. He pulled out a kitchen chair and sank down, bending his tall, lanky frame. "I'm not the second coming, Johnny."

Winchester exhaled loudly through his nose. "To my kid you are." He studied the tequila label. "What were you thinking?"

Caleb shrugged his shoulders. "I figure you let the kid drive a car. . ."

"He isn't licensed!" John interjected in exasperation. "And he only drives in an emergency."

Reaves raised his eyebrows, trying hard to hide the chuckle that wanted to escape. It was funny how people could put a spin on the truth to justify their actions. An emergency consisted not only when John was wounded, but when he was too drunk to find his way home. "He doesn't need a license for what he was doing." Caleb cleared his throat. "Ahh, what gave it away?"

"Dean smelled like cheap perfume and that shit-eating grin on his face." The older hunter took another swig of tequila. He opened his mouth and exhaled the heated liquor. "Tell me he used protection."

"Yeah, the first time, definitely," Caleb nodded.

"Reaves!" John barked, slamming the bottle on the table, causing the beer to jump to a rattled attention.

Caleb reached for the tequila bottle. "Yes, he did, no one's making you a grandfather any time soon." He took a mouthful, and passed the bottle back to the older hunter. "How old were you?"

John shook his head and grinned.

Caleb jutted out his chin in persistence.

The eldest Winchester relented, "Seventeen."

Caleb bowed his head, but still laughed. "Well, I guess Dean broke the Winchester family record." He knocked twice on the blue Formica table top. "I was 15."

"And look how you turned out."

Reaves sobered at the insult. He had overcome adversity and taint to be a semi, well adjusted person. No one could take away his strength of character. "Great, if I do say so myself."

John leaned against the kitchen cabinets. Caleb knew he purposely was not taking a seat at the kitchen table so that he could continue to scold the younger hunter. "My kid could do a lot better for a role model."

The younger hunter ran through the list of men in the brotherhood in his mind. "He could do a whole hell of a lot worse, unless you want Dean to be a priest?"

John paused for a moment. "Maybe Sammy," he said thoughtfully.

"You wish!" Caleb exclaimed incredulously. "Once puberty hits that kid. . ." Reaves let the thought trail off, trying to imagine a grown up Sam. He couldn't see past the baby fat just yet.

The older hunter took another mouthful of tequila, placing the bottle in the crook of his arm and groaned. "Why are you threatening me?"

Caleb didn't know if the tequila was helping or if John was just being rational about the inevitable loss of Dean's virginity. Looking at the bottle, down by a quarter of its amount, Reaves deduced it was the liquor.

"You're corrupting my kid."

"Thought demon hunting did that." Caleb sat straighter in his chair. "Sex is good, clean fun, well most of the time. Sometimes a little. . ." Reaves thought about the time he was with the twins in Nebraska. He really needed to go back to Nebraska soon.

"You're thinking with the downstairs brain not the upstairs brain." John murmured then snapped his fingers to bring the family friend back to the present discussion. "What's done is done."

Reaves noticed the beer on the table. He grabbed the carton, and brought it to the refrigerator, breaking off one of the bottles, and placing it in the freezer to immediately chill. "Gonna tell Mac about this?"

"I might," John swirled the bottle of tequila, and set it down.

Caleb rifled through the cabinets, looking for a quick snack of potato chips. The cabinets were bare. He returned to the freezer, pulling out the cool beer. He hit the top against the kitchen counter until the cap popped off. "Hell, Bobby took me to this dive in Montana my first time and told me to have at it."

"Bobby?" John sat in the seat vacated by the younger hunter.

"Well, you think Jim was going to volunteer?" Caleb took a drink from the bottle, and swallowed it, feeling refreshed even though the Budweiser was not perfectly cold.

"No." John rubbed the stubble on his chin with a grin. "There's going to be no living with him."

Caleb wondered again, how well his friend knew his own children. Dean was growing up, and his confidence and cockiness was something that needed to be cultivated to help protect him later. Maybe it was Reaves speaking from experience or the sinking knowledge that in being the protector of the Winchester family, Dean would face many challenges that could break him. "He'll be fine. He's living every American boy's dream - fast cars, fast women, and violence."

The older hunter stood up, stretching and yawning. "You are never taking my kid to Alabama either . . . probably end up getting him married."

Caleb smirked, feeling tiredness overtaking him. "Funny, that actually came up."

The end


End file.
